86971-64-4Relevant articles and documents
A General and Robust Method for the Preparation of (E)- and (Z)-Stereodefined Fully Substituted Enol Tosylates: Promising Cross-Coupling Partners
Ashida, Yuichiro,Sato, Yuka,Honda, Atsushi,Nakatsuji, Hidefumi,Tanabe, Yoo
supporting information, p. 4072 - 4080 (2016/11/26)
A robust method for preparing (E)- and (Z)-stereodefined fully substituted enol tosylates is described. α-Substituted β-keto esters undergo (E)-selective enol tosylations using TsCl-Me2N(CH2)6NMe2 as the reagent (method A, 13 examples; 63-96%) and (Z)-selective enol tosylations using TsCl-TMEDA-LiCl as the reagent (method B, 13 examples; 62-99%). A plausible mechanism for the (E)- and (Z)-enol tosylation selectivity is proposed. A 1H NMR monitoring experiment revealed that TsCl coupled with TMEDA formed a simple N-sulfonylammonium intermediate.
Stereoselective synthesis of new chiral N-tertiary tetrasubstituted β-enamino ester piperidines through an ammonia-catalyzed process
Calvet-Vitale, Sandrine,Vanucci-Bacque, Corinne,Fargeau-Bellassoued, Marie-Claude,Lhommet, Gerard
, p. 2071 - 2077 (2007/10/03)
We report here two approaches for the preparation of new N-substituted β-enamino ester piperidines featuring an exocyclic tetrasubstituted double bond, based either on the direct alkylation of piperidine β-enamino esters bearing an exocyclic trisubstitute
Improved procedure for the Blaise reaction: A short, practical route to the key intermediates of the saxitoxin synthesis
Hannick,Kishi
, p. 3833 - 3835 (2007/10/02)
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